US2127841A - Condensation products of high mo- - Google Patents
Condensation products of high mo- Download PDFInfo
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- US2127841A US2127841A US2127841DA US2127841A US 2127841 A US2127841 A US 2127841A US 2127841D A US2127841D A US 2127841DA US 2127841 A US2127841 A US 2127841A
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- higher molecular
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- 239000007859 condensation product Substances 0.000 title description 24
- 239000000047 product Substances 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 32
- 125000001183 hydrocarbyl group Chemical group 0.000 description 28
- 239000002253 acid Substances 0.000 description 24
- 125000001931 aliphatic group Chemical group 0.000 description 24
- 239000000463 material Substances 0.000 description 24
- 125000003277 amino group Chemical group 0.000 description 18
- 239000004753 textile Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000004429 atoms Chemical group 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atoms Chemical group C* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- -1 unsaturated fatty acid chlorides Chemical class 0.000 description 8
- 238000009736 wetting Methods 0.000 description 8
- 102100001249 ALB Human genes 0.000 description 6
- 101710027066 ALB Proteins 0.000 description 6
- 229940050528 albumin Drugs 0.000 description 6
- 239000005018 casein Substances 0.000 description 6
- 235000021240 caseins Nutrition 0.000 description 6
- XXGJRAFLOAKNCC-UHFFFAOYSA-N methane;molecular hydrogen Chemical compound C.[H][H] XXGJRAFLOAKNCC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 239000001828 Gelatine Substances 0.000 description 4
- 210000003284 Horns Anatomy 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920001184 polypeptide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 2
- IQNKUQDXFKGYSX-UHFFFAOYSA-N 2-chloro-N-dodecylacetamide Chemical compound CCCCCCCCCCCCNC(=O)CCl IQNKUQDXFKGYSX-UHFFFAOYSA-N 0.000 description 2
- WOHIIBNOBPKOGA-UHFFFAOYSA-N 2-sulfotetradecanoic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)S(O)(=O)=O WOHIIBNOBPKOGA-UHFFFAOYSA-N 0.000 description 2
- IHPIMSWIZFEMGZ-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)N(C1=CC=CC=C1)CC(=O)Cl Chemical compound C(CCCCCCCCCCC)(=O)N(C1=CC=CC=C1)CC(=O)Cl IHPIMSWIZFEMGZ-UHFFFAOYSA-N 0.000 description 2
- XRZFQMXYVDXQHB-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)NC(C(=O)Cl)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCC)(=O)NC(C(=O)Cl)C1=CC=CC=C1 XRZFQMXYVDXQHB-UHFFFAOYSA-N 0.000 description 2
- RUPCKVFWTHBWMY-UHFFFAOYSA-N C(CCCCCCCCCCC)N(C1=CC=CC=C1)CC(=O)Cl Chemical compound C(CCCCCCCCCCC)N(C1=CC=CC=C1)CC(=O)Cl RUPCKVFWTHBWMY-UHFFFAOYSA-N 0.000 description 2
- LCPYQJIKPJDLLB-UWVGGRQHSA-N Leu-Leu Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CC(C)C LCPYQJIKPJDLLB-UWVGGRQHSA-N 0.000 description 2
- IGAVWBXNNIYVOB-UHFFFAOYSA-N S(=O)(=O)(O)C(C(=O)Cl)CCCCCCCCCCCC Chemical compound S(=O)(=O)(O)C(C(=O)Cl)CCCCCCCCCCCC IGAVWBXNNIYVOB-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N Thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BIIPHRRRSVZMLK-UHFFFAOYSA-N decanoyl bromide Chemical compound CCCCCCCCCC(Br)=O BIIPHRRRSVZMLK-UHFFFAOYSA-N 0.000 description 2
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 2
- ZZRCKSSPGJOTEE-UHFFFAOYSA-L disodium;carbamoyl phosphate Chemical class [Na+].[Na+].NC(=O)OP([O-])([O-])=O ZZRCKSSPGJOTEE-UHFFFAOYSA-L 0.000 description 2
- JPPYCWJDINILKY-UHFFFAOYSA-N dodecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCOC(=O)CCl JPPYCWJDINILKY-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- RSRQBSGZMPVCOI-UHFFFAOYSA-N hexadecyl propanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CC RSRQBSGZMPVCOI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 108010091798 leucylleucine Proteins 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/76—Albumins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/0005—Vertebrate antigens
- A61K39/0008—Antigens related to auto-immune diseases; Preparations to induce self-tolerance
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/02—Organic and inorganic agents containing, except water
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/06—Protein or carboxylic compound containing
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Organic Chemistry (AREA)
- Rheumatology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Aug. 23, 1 938 CONDENSATION PRODUCTS OF HIGH M0- LEOULAR ALBUBHNOEJS SPLIT PRODUCTS many, a corporation of Germany No Drawing. Application January 15, 1935, Se-
rial No. 1,900. In Germany January 16, 1934 7 Claims.
This invention relates to compounds having wetting and cleansing properties rendering them excellently adapted for use in the treatment of textile materials.
In accordance with a process already known to the art, albuminous split productsare condensed with higher molecular fatty acids orhigher molecular organic sulfonic acids, or with their derivatives, to produce products suitable for use principally in the finishing of various fibrous materials. Such process is disclosed in the Sommer Patent No. 2,015,912 wherein there is disclosed treating high molecular split off products of albumin particularly those of the lysalbinic acid and protalbinic acid type, with higher saturated or unsaturated fatty acid chlorides.
The object of the present invention is to produce products which are in some respects similar to those of the said patent but which possess superior properties as will hereinafter be described.
In accordance with the present invention, condensation products having unusually effective properties are obtained from the higher molecular split products of the nature of those described in the above mentioned patent by condensing such products under alkaline conditions in conventional manner with certain compounds containing at least one higher molecular aliphatic group in the molecule, a halogen atom in a readily reactive condition and at least one other modifying radical as will hereinafter be disclosed.
According to one embodiment of the present invention, the compounds used possess the general formula:
HalogenC (R1122) CO--X wherein X stands for a OR3 group or a N(R3R4) group and at least one of the groups R1 to R4 stands for a higher molecular aliphatic group and the remaining three groups stand for hydrogen or a hydrocarbon group.
Such compounds are e. g. the esters and the amides of lac-halogen fatty acids wherein it is essential that in the molecule-either in the acid component or in the alcohol component or in the amido-group-there be a higher molecular aliphatic alkyl-residue. As components for the 0 reaction with the albuminous products there may be considered e. g. chloro acetic-acid lauryl-ester, oc-bIOIl'iO propionic-acid-cetyl-ester, a-bromolauric acid-oleyl-ester, di-chloro carbonic acidester of 1,18-steary1ene-glycol, chloro acetic acid- N-laurylamide, chlor-acetic acid- (N-cetylphenyl) -amide, oc-bIOl'llO-lSMIiC acid-oleyl-amide, dilauryl-carbamide-chloride and others.
Among the albuminous split-products adapted to form the valuable high molecular fatlike products capable of being condensed with the said organic compounds which in the alkyl-residue may also contain any substituents such as halogen, hydroxyl, free or substituted amino-groups, there are the diand polypeptides to be mentioned such as e. g. the leucyl-leucine, silk-fibroine and others, derivates of albumin such as lysalbinic acid, separation-products of size, casein, gelatine, leather, horn etc., which products may be described collectively as the water soluble higher molecular products of simple hydrolysis of albuminous materials containing amino groups with a replaceable hydrogen atom. As to the condensation one proceeds in the following way: The albuminous split-products are dissolved or emulsified in slightly alkaline aqueous media, whereupon one adds the halogen compound under vigorous stirring, taking care that a slightly alkaline reaction is always prevailing. The reaction temperatures may be between -20 and +150 but generally the reaction takes place at 5-35", whereby it is sometimes advantageous to let the temperature subsequently rise to about 70-80". The reaction takes place by the union of the amino group of the albuminous derivative with the halogenated atom of the molecule containing the higher molecular alkyl group, thereby liberating halogen halide.
Furthermore the organic carbonic acid halogenides of the general formula halogen-CO-R Y-R are likewise suitable as condensable compounds for the condensation with higher molecular albuminous split-products. In the said formula, R means an alkyleneor arylene residue and R any hydrocarbon residue, with the understanding that one of same contains no less than 8 C-atoms in an aliphatic chain. The hydrocarbon residues may furthermore contain some substituents such as halogen, amino, hydroxyl. The symbol Y stands for the elements 0 or S respectively or the atom-groups S02, NR CONRZ NRFCO or NR' SO2, wherein R" means hydrogen or any hydrocarbon residue. Such compounds are e. g. the ethers and thio-ethers of carbonic acid halogenides, alkyl-sulfo-carbonic-acid halogenides, alkyl-amino-carbonic-acid halogenides, substituted carbon-amide-carbonic-acid halogenides, acidyl-amino-carbonic-acid halogenides and N-alkylsulfamide-carbonic-acid halogenides, wherein it is, however, necessary that at least one higher molecular aliphatic hydrocarbon residue with no less than 8 C-atoms is always present in the total molecule. -As components for the condensation with albuminous split-products such as di and poly-peptides, albumin derivates, separation-products of size, casein, horn, leather etc. may be considered e. g. w-butylor c'yclo-hexylether of capric acid-chloride, lauroxy-acetic-acid bromide, w-piperidino undecylene-acid chloride, N-lauryl-phenylamino-acetic-acid-chloride, ocphenyl-thio-laurin acid bromide, ,B-cetyl-thiopropionic acid chloride, dodecyl-sulfo-acetic acid chloride, N-diocetyl-adipic acid-amide-acid chloride, N -lauroyl-phenyl-amino-acetic acid chloride, N,N-dodecyl-p-toluol-sulfonyl-amino-acetic acid chloride and others.
The condensation of these compounds with the albuminous split-products is done in the usual way in alkaline media and under the same conditions as described above.
Example 1 130 weight-parts of technical lysalbinic acid sodium salt are dissolved in 150-200 parts of water. Thereupon one adds gradually, under stirring, 80 parts by weight of chlor-acetic acid- N-clilaurylamide. At the same time one adds parts by weight of a 33% solution of caustic soda. The reaction temperature is kept for some hours at -30", whereupon one heats the mass to 60-70 for a short period. The reaction product can be worked in the well-known manner, by evaporating in vacuo, to form a paste ready for use or a dry powder.
By adding the thus obtained reaction product at the rate of 2 g. per litre to an aqueous washing bath or to an alkaline textile treatment bath, one secures an excellent cleansing or wetting effeet or an equalizing effect, respectively.
It is also remarkable that the aforedescribed products impart to the thus treated textile-materials an enhanced protection against deterioration.
Example 2 By adding to a dyeing-bath 1-2 g. per litre of a condensation product obtainable through the combination of 39 parts by weight of lysalbinic acid sodium salt dissolved in 10-times its weight of water with 26 parts by weight of N- lauroyl-phenylamino-acetic acid-chloride with an addition, at -40 C., of 6 parts by weight of a 33% solution of caustic soda, one secures a uniform distribution of color in the material.
Example 3 In condensing the di-sodium salt of thioglycolic acid with dodecyl-chloride in the wellknown manner and in thereafter oxydizing the sulfide obtained by means of an aqueous nitric acid solution, there results the dodecyl-sulfoacetic acid, which after converting into the acid chloride permits an easily effected condensation, according to the well-known method, with splitproducts of casein or gelatine leading to the formation of high molecular products. The lat ter are gained either in the form of concentrated aqueous solutions or of condensed pastes or of easily soluble light yellow to light brown powders.
By an addition of 03% of this condensation product to a washing-bath one obtains with textile materials an excellent wetting and cleansing effect.
Of a similar efiect is e. g. also a condensation product obtainable from the w-butyl-ether of capric acid bromide and lysalbinic acid sodium salt. It is remarkable that to materials treated with the aforedescribed condensation products an enhanced protection is imparted against chemical and mechanical influences.
What I claim is:- I
1 Textile treating agents consisting of the alkaline condensation products of water soluble higher molecular products of simple hydrolysis albuminous materials containing amino groups with a replaceable hydrogen atom, with a compound selected from the group consisting of the compounds of the general formula HalogenC R1R2) COX wherein X stands for a -OR3 group or a -N(R3R4) group, at least one of the R1, R2, R3 and R4 groups stands for a higher molecular aliphatic group, the remaining three Rs being hydrogen or a hydrocarbon group, and compounds of the general formula wherein R5 stands for a hydrocarbon group and Rs stands for a hydrocarbon group and at least one of the two groups contains no less than 8 carbon atoms in an aliphatic hydrocarbon chain, and wherein Y stands for one of the atoms or atom groups 0, S, S02, NR7, CONRv, NRqCO or NRvSOz, wherein R1 stands for hydrogen or a hydrocarbon group.
2. New compounds consisting of the alkaline condensation products of water soluble higher molecular products of simple hydrolysis of albuminous materials containing amino groups with a replaceable hydrogen atom, with compounds of the general formula wherein X stands for a member of the group consisting of a OR3 group and a N(R3R4) group, at least one of the R1, R2, R3 and R4 groups standing for a higher molecular aliphatic group, the remaining three Rs being selected from hydrogen and hydrocarbon groups.
3. Textile treating agents having wetting and cleansing properties which consist in the alkaline condensation products of water soluble higher molecular products of simple hydrolysis of albuminous materials containing amino groups with a replaceable hydrogen atom, with compounds of the general formula wherein R5 stands for a hydrocarbon group and Rs stands for a hydrocarbon group and at least one of the two groups contains no less than 8 carbon atoms in an aliphatic hydrocarbon chain, and wherein Y stands for one of the atoms or atom groups 0, 6, S02, NR1, CONRv, NRqCO or NR'1SO2, wherein R7 stands for hydrogen or a hydrocarbon group.
4. The textile treating agent consisting of the alkaline condensation product of the sodium salt of lysalbinic acid with chlor-acetic acid-N- di-lauryl-amide.
5. Textile treating agents which consist in the alkaline condensation products of water soluble higher molecular products of simple hydrolysis of albuminous materials containing amino groups with a replaceable hydrogen atom, with compounds of the general formula HalogenCON(RsR4) wherein at least one of the groups R3 and R4 is a higher aliphatic group while the remaining group comprises a member of the group consisting of hydrogen and hydrocarbon groups.
6. The composition for use in the treating of textile materials of the general formula ZC(R R )COX, wherein Z represents a radical of a water soluble higher molecular protein group obtained by simple hydrolysis of an albuminous compound containing at least one amino group and X represents a member of the group consisting of OR and -NR R and wherein at least one of the R R R and R groups stands for a higher molecular aliphatic group, the remaining three Rs being selected from hydrogen and hydrocarbon groups.
'7. The composition for use in the treating of textile materials of the general formula ZCOY, wherein Z represents a radical of a water soluble higher molecular protein group obtained by simple hydrolysis of an albuminous compound containing at least one amino group and Y represents NR R wherein R is a higher molecular aliphatic group and R is hydrogen.
WALTER GELLENDIEN
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2127841A true US2127841A (en) | 1938-08-23 |
Family
ID=3429616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2127841D Expired - Lifetime US2127841A (en) | Condensation products of high mo- |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2127841A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2523324A (en) * | 1947-04-23 | 1950-09-26 | United Shoe Machinery Corp | Tanning with esters of chloroformic acid in an nonaqueous medium |
| US2523325A (en) * | 1947-07-10 | 1950-09-26 | United Shoe Machinery Corp | Tanning in a nonaqueous medium |
| DE1059912B (en) * | 1956-06-14 | 1959-06-25 | Chem Fab Gruenau Veb | Process for the production of amphoteric surface-active protein compounds |
| US4406833A (en) * | 1982-06-04 | 1983-09-27 | Fats And Proteins Research Foundation, Inc. | Surfactants derived from fatty acid esters and proteinaceous material |
| US4713446A (en) * | 1985-09-06 | 1987-12-15 | Minnesota Mining And Manufacturing Company | Viscoelastic collagen solution for ophthalmic use and method of preparation |
| US4851513A (en) * | 1985-09-06 | 1989-07-25 | Minnesota Mining And Manufacturing Company | Viscoelastic collagen solution for opthalmic use and method of preparation |
| US4883864A (en) * | 1985-09-06 | 1989-11-28 | Minnesota Mining And Manufacturing Company | Modified collagen compound and method of preparation |
| US5071960A (en) * | 1989-09-07 | 1991-12-10 | Hoechst Aktiengesellschaft | High molecular weight protein/fatty acid condensation products which are very well tolerated by the skin and mucosa |
-
0
- US US2127841D patent/US2127841A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2523324A (en) * | 1947-04-23 | 1950-09-26 | United Shoe Machinery Corp | Tanning with esters of chloroformic acid in an nonaqueous medium |
| US2523325A (en) * | 1947-07-10 | 1950-09-26 | United Shoe Machinery Corp | Tanning in a nonaqueous medium |
| DE1059912B (en) * | 1956-06-14 | 1959-06-25 | Chem Fab Gruenau Veb | Process for the production of amphoteric surface-active protein compounds |
| US4406833A (en) * | 1982-06-04 | 1983-09-27 | Fats And Proteins Research Foundation, Inc. | Surfactants derived from fatty acid esters and proteinaceous material |
| US4713446A (en) * | 1985-09-06 | 1987-12-15 | Minnesota Mining And Manufacturing Company | Viscoelastic collagen solution for ophthalmic use and method of preparation |
| US4851513A (en) * | 1985-09-06 | 1989-07-25 | Minnesota Mining And Manufacturing Company | Viscoelastic collagen solution for opthalmic use and method of preparation |
| US4883864A (en) * | 1985-09-06 | 1989-11-28 | Minnesota Mining And Manufacturing Company | Modified collagen compound and method of preparation |
| US5071960A (en) * | 1989-09-07 | 1991-12-10 | Hoechst Aktiengesellschaft | High molecular weight protein/fatty acid condensation products which are very well tolerated by the skin and mucosa |
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